Flavor improving agent

ABSTRACT

Disclosed is a flavor improving agent that is a fraction derived from fruit juice or squeeze. A fraction wherein the amount of substance ratio between polyphenols and saccharides, the latter after acid hydrolysis of the fraction, (polyphenol/saccharide) is 0.1-10, and even more preferably, wherein the amount of substance ratio of the polyphenol and the saccharide before acid hydrolysis of the fraction (polyphenol/saccharide) is 1-100, and is used as a flavor improving agent. Such fraction are obtained with a method such as by a fruit juice or squeeze being absorbed onto a synthetic resin adsorbent and the adsorbed components being eluted by a solvent, or by extracting fruit juice or squeeze with ethanol. The flavor improving agent has flavor improving effects such as suppressing sourness, bitterness and astringency of foods and beverages, reducing harsh taste, contributing to a juice-like feel and contributing to a richness. In addition to foods and beverages, the flavor improving agent can also be added to pharmaceutical products or oral care products and the like, as well as to flavor composition.

TECHNICAL FIELD

The present invention relates to a flavor improving agent containing afraction derived from fruit juice, which gives a juice-like feel orremoves or reduces unpleasant tastes which foods and beverages have.

BACKGROUND ART

When eating foods or taking beverages, we feel various tastes amongwhich are included tastes felt as unfavorable tastes. Bitterness,astringency, harsh taste, and the like are generally received asunfavorable tastes in many cases. Sourness is in some cases received asa favorable taste, but sourness with tongue-biting stimulus is receivedas an odd taste and is not acceptable for us. An attempt to suppress orreduce these unfavorable tastes has conventionally been made. Further,to the contrary, an attempt to enhance a juice-like feel or a volumefeeling of foods and beverages, which are considered as favorabletastes, has been made as well.

As a method for improving the flavor of such foods and beverages,various methods such as methods of using fruits, fruit juices, squeezesor ingredients of fruits or fruit juices have also been known. As someof these methods, there are illustrated, for example, a method ofreducing sourness or bitterness of foods by using a cranberry juiceconcentrate which has been subjected to decolorizing treatment andelectrodialyzing treatment (see Patent Document 1), a method of giving amore natural body, a richness, and a thickness to foods and beverages byusing vicenin-2 as an active ingredient (see Patent Document 2), amethod of improving flavor of protein foods by adding an extract ofgrape seeds or grape skins (see Patent Document 3), a method of reducingvarious unfavorable smells and tastes of foods and beverages andimproving flavor thereof by adding a hesperidin glycoside or a mixtureof hesperidin glycoside and hesperidin (see Patent Document 4), a methodof masking an astringent taste or a saltiness by compounding a berry inan oral composition containing hydroxycitric acid (see Patent Document5), and a method of enhancing a richness, juiciness, body, and mildnessto a taste of foods and beverages or of a composition for oral cavity byadding a high-boiling point fraction obtained in a dewaxing treatment ofa citrus cold press oil (see Patent Document 6).

However, with the method of using a cranberry fruit juice concentratedescribed above, the process for preparing the raw material is socomplicated that the method involves a problem in view of productioncost. Also, with the method of using vicenin-2 as an active ingredient,an extent of the flavor-improving effect is limited, and a wider extentof the flavor-improving effect is demanded. Further, with the method ofusing an extract of grape seeds or grape skins, its application islimited to improvement of flavor of protein foods, thus the methodinvolving a problem that its application is limited. The method of usinga hesperidin glycoside or a mixture of hesperidin glycoside andhesperidin involves a problem that its flavor-improving effect isinsufficient. The method of compounding a berry described above involvesa problem that kinds of flavor to be improved are limited. The method ofusing a high-boiling point fraction obtained in a dewaxing treatment ofa citrus cold press oil involves a problem that, since the flavorimproving agent is an oil-soluble material, its application is limited.

As mentioned above, various methods for improving flavor of foods byusing fruits, fruit juices, fruit juice ingredients, and the like havebeen conventionally known. However, these methods involve such problemas that foods to be used are limited, that the production process iscomplicated, or that the flavor-improving effect is insufficient. Aflavor improving agent, therefore, is demanded which can exhibit itseffects even when added to foods in only a small amount, which givesalmost no taste or smell, which has a high safety, which can be producedat a low cost, and which can be widely used with respect to kinds offoods and beverages to be applicable and kinds of flavors to beimproved. Such improvement of flavor is not limited only to foods andbeverages but is required with pharmaceutical products to be used asoral compositions, oral care products, and the like as well. Also, byincorporating a flavor improving agent in a flavor composition which isused for these various products, flavor-improving effects can be givento the various products together with favorable aroma.

Additionally, it has been conventionally known to remove unpleasantsmells liable to generate during storage of fruit juices by using anonionic porous polymer resin (see Patent Document 7). However, it havenot been confirmed that fruit juice components adsorbed on the resinhave flavor-improving effects. It has also been known to produce anatural flavor by adsorbing aroma ingredients of fruit juice on a porouspolymer resin and recovering it (see Patent Document 8). However, sinceits object is to recover an aroma, it is impossible to conduct removalof a solvent by distillation or conduct a heating, which cause lost oflow-boiling point ingredients and thermal change of aroma.

PRECEDING TECHNICAL DOCUMENTS Patent Documents

-   [Patent Document 1] JP-A 10-42824-   [Patent Document 2] JP-A 2006-238829-   [Patent Document 3] JP-A 11-75708-   [Patent Document 4] JP-A 11-318379-   [Patent Document 5] JP-A 10-52239-   [Patent Document 6] JP-A 2003-299459-   [Patent document 7] JP-A 47-23562-   [Patent Document 8] JP-B 48-34234

SUMMARY OF THE INVENTION Problems to be Solve by the Invention

The present invention has been made in view of the current circumstancesabove. An object of the invention, therefore, is to provide a flavorimproving agent which can solve the conventional problems describedabove and, more specifically, to provide a flavor improving agent whichcan be produced by a simple method at a low production cost, which canexhibit a high flavor-improving effect even when added in only a smallamount, which can give almost no taste or smell, which has a highsafety, and which is applicable to a wide extent of products and has awide extent of flavor-improving effects.

Further, another object of the invention is to provide a flavorcomposition, foods and beverages, pharmaceutical products and oral careproducts, whose flavors are improved.

Means for Solving the Problems

After intensive studies to solve the aforementioned problems, thepresent inventors have found that a specific fraction derived from fruitjuice or squeeze, for example, a specific fraction obtained by bringingfruit juice or squeeze into contact with a synthetic resin adsorbent andthen eluting the ingredient adsorbed on the synthetic resin adsorbentwith a solvent, shows excellent effects as a flavor improving agent andthe invention have been completed based on this finding.

That is, the invention relates to the following flavor improving agent,and a flavor composition, foods and beverages, pharmaceutical products,and oral care products containing the flavor improving agent.

[1] A flavor improving agent comprising a fraction derived from fruitjuice or squeeze, wherein the amount of substance ratio betweenpolyphenols and saccharides, the latter after acid hydrolysis of thefraction, (polyphenol/saccharide) is 0.1 to 10.[2] The flavor improving agent described above, wherein the amount ofsubstance ratio between polyphenols and saccharides before acidhydrolysis of the fraction, (polyphenol/saccharide) is 1 to 100.[3] The flavor improving agent described in [1] or [2] above, whereinthe fraction is obtained by adsorbing fruit juice or squeeze onto asynthetic resin adsorbent and then eluting the adsorbed ingredients witha solvent.[4] The flavor improving agent described in any one of [1] to [3],wherein the fraction is an ethanol extract of fruit juice or squeeze.[5] The flavor improving agent described in any one of [1] to [4],wherein the fruit is at least one member selected from among orange,lemon, grapefruit, lime, blueberry, strawberry, apple, pear, grape,melon, pineapple, peach, mango, and banana.[6] The flavor improving agent described in any one of [1] to [5],wherein the flavor improving effect is at least one of suppressingsourness, bitterness or astringency, reducing harsh taste of vegetables,giving juice-like feel, and giving a richness.[7] A flavor composition containing a flavor improving agent describedin any one of [1] to [6] above.[8] Foods and beverages containing a flavor improving agent described inany one of [1] to [6] above.[9] A pharmaceutical product containing a flavor improving agentdescribed in any one of [1] to [6] above.[10] An oral care product containing a flavor improving agent describedin any one of [1] to [6] above.

Advantageous Effects of the Invention

The flavor improving agent of the present invention can be produced by asimple procedure of adsorbing fruit juice or squeeze onto a syntheticresin adsorbent and then desorbing ingredients adsorbed on the syntheticresin adsorbent with a solvent, or of extracting fruit juice or squeezewith ethanol. In addition, as the starting material is fruit juice orsqueeze, the flavor improving agent of the present invention isexcellent in safety. The resulting flavor improving agent, therefore,can be used for a wide extent of products such as flavor compositions,foods and beverages, pharmaceutical products, oral care products, andthe like to suppress their unfavorable tastes such as astringency,bitterness, and harsh taste. Further, the flavor improving agent canenhance favorable tastes such as improvement of a composite flavor oftaste and smell, giving fruit-like feel and giving a richness. Thus, theflavor improving agent can be applied wider products and improve variouskinds of flavor.

MODE FOR CARRYING OUT THE INVENTION

The flavor improving agent of the present invention and the process forobtaining it will be described hereinafter.

As a raw material for the flavor improving agent of the invention, fruitjuice or squeeze is used. Fruits to be used as raw materials in theinvention are not particularly limited and any one that is known asfruit can be used. To illustrate some of them, there are illustrated,for example, citrus fruits (e.g., orange, lemon, grapefruit, satsumamandarin, Citrus maxima, Citrus natsudaidai, Citrus hassaku, lime,Citrus medica, Citrus junos, sweetie, Citrus sudachi, Citrussphaerocarpa, Fortunella, etc.), berries (e.g., raspberries such asraspberry, blackberry, loganberry, youngberry, boysenberry, tayberry,cloudberry, salmonberry, arctic raspberry, mayberry, etc.; cowberriessuch as blueberry, cranberry, cowberry, etc.; currants such asgooseberry, red-currant, black-currant, etc.; silverberry; mulberry;strawberry; wolfberry; elderberry; etc.), pears (e.g., pear, Japanesepear, Chinese pear, etc.), apple, grape, pineapple, fig, melon, mango,pomegranate, passion fruit, litchi, banana, peach, watermelon, tomato,papaya, guava, Japanese medlar, and the like. As these fruit juices orsqueeze, those which are commercially available may be used itself ormay be directly obtained from fruits by, for example, incorporating afruit juice- or squeeze-obtaining step as one step in a productionprocess of obtaining the flavor improving agent. Further, sincecommercially available fruit juices or squeezes often contain solidmaterials such as fruit fibers, a treatment for removing the solidmaterials may be conducted using, for example, a filtering apparatusused in the production of foods, such as a press filter, a vacuumfilter, a basket centrifugal filter or a separation plate typecentrifugal filter. Additionally, in such treatment, a filtration aid orthe like may be used as needed. These fruit juices or squeezes may beused alone or as a mixture of two or more thereof.

In the invention, a specific fraction obtained by subjecting theaforementioned fruit juice or squeeze to an appropriate treatment, i.e.,a fraction wherein the amount of substance ratio between polyphenols andsaccharides, the latter after acid hydrolysis of the fraction,(polyphenol/saccharide) is 0.1 to 10 is used as a flavor improvingagent. The fraction is preferably a fraction wherein the amount ofsubstance ratio between polyphenols and saccharides before acidhydrolysis of the fraction, (polyphenol/saccharide) is 1 to 100. Suchfraction can be obtained by, for example, the following processes.However, the process for obtaining the specific fraction of theinvention derived from fruit juice or squeeze is not limited only tothese processes.

As a preferred process for obtaining the flavor improving agent of theinvention, there is illustrated firstly a process of adsorbing fruitjuice or squeeze onto a synthetic resin adsorbent and then desorbing theadsorbed ingredients with a solvent. As this process, a process ofallowing fruit juice or squeeze to pass through the column in whichsynthetic resin adsorbent particles are filled as a fixing carrier toadsorb the fruit juice ingredients or squeeze ingredients onto theparticles and then eluting the adsorbed fraction with a solvent torelease the ingredients is preferably employed.

This process will be explained more specifically below. First, fruitjuice or squeeze as it is or that after adjusting to an arbitraryconcentration with water is allowed to pass through the column filledwith the synthetic resin adsorbent particles. As the synthetic resinadsorbent used, there can be exemplified adsorbents composed of aromaticresins, acrylic resins, acrylonitrile series resins or the like. Suchsynthetic resin adsorbents are commercially available and there areillustrated, for example, DIAION HP20 and HP21, and SEPABEADS SP70(these being aromatic resins and manufactured by Mitsubishi Chemical)(“DIAION” and “SEPABEADS” being registered trademarks; hereinafter thesame), SEPABEADS SP825, SP850 and SP700 (these being aromatic highsurface area resins and manufactured by Mitsubishi Chemical), SEPABEADSSP207 (aromatic modification resin; manufactured by MitsubishiChemical), DIAION HP20SS and SEPABEADS SP20SS and SP207SS (these beingaromatic small-particle resins and being manufactured by MitsubishiChemical), AMBERLITE XAD2, XAD4, FPX66, XAD1180, XAD1180N, and XAD 2000(these being styrene series resins and being manufactured by OrganoCorporation) (“AMBERLITE” being a registered trademark; hereinafter thesame), DIAION HP2MG (acrylic resin; manufactured by MitsubishiChemical), AMBERLITE XAD7HP (acrylic resin; manufactured by OrganoCorporation), Sephadex LH20 (cross-linked dextran derivative;manufactured by GE Healthcare Bioscience) (“Sephadex” being a registeredtrademark), and the like. As the synthetic resin adsorbent, anappropriate one may be selected according to a kind or concentration ofthe fruit juice or squeeze to be use, which is to be allowed to passthrough the column, or according to co-existing substances therein.

The amount of the synthetic resin adsorbent varies depending upon sizeof the column, an amount of fruit juice or squeeze to be allowed topass, concentration of fruit juice or squeeze, a kind of solvent to beused, a kind of adsorbent to be used, and the like. An amount whichprovides optimal results, therefore, may be employed in consideration ofthese conditions, thus a preferred range thereof in a general sense notbeing determined. Usually, it suffices to use a 0.1- to 100-fold amount(by mass) of a synthetic resin adsorbent based on the soluble solidingredients in fruit juice or squeeze to be allowed to pass sincepreferred results can usually be obtained when allowed to pass fruitjuice or squeeze containing a 0.01- to 10-fold amount (by mass) ofsoluble solid components based on the synthetic resin adsorbent.However, preferred ranges of the amount of fruit juice or squeeze to beallowed to pass and of the amount of synthetic resin adsorbent to beused are not limited only to the above-described ranges. Further, theconcentration of fruit juice or squeeze to be allowed to pass is notparticularly limited but, when the concentration of fruit juice orsqueeze is high, the pass-through speed cannot be increased so much dueto the high viscosity thereof, a preferred fruit juice concentration isBx. 50 or less, more preferably Bx. 20 or less.

Ingredients having the flavor improving effect in the fruit juice orsqueeze are adsorbed to the absorbent by allowing the fruit juice orsqueeze to pass through the aforementioned column. The pass-throughamount and the pass-through speed of the fruit juice or squeeze varydepending upon size of the column, a kind of the synthetic resinadsorbent to be used, a kind of fruit juice or squeeze to be allowed topass, and concentration of fruit juice or squeeze to be allowed to passbut, usually, SV=20 or less is preferred. After allowing fruit juice orsqueeze to pass through the column, it is preferred to allow water topass through the column to wash for removing fruit juice or squeeze andingredients of the fruit juice or squeeze, which were not adsorbed tothe resin but remaining in the column.

The ingredients adsorbed on the adsorbent resin are eluted and releasedby allowing a solvent to pass through the column. The eluting solvent ispreferably selected from among water, ethanol, methanol, acetone, ethylacetate, and a mixture thereof. Of these an ethanol-water mixed solventis particularly preferred. In addition, it is more preferred to use a50/50 to 99.5/0.5 (volume/volume) ethanol-water mixed solvent in orderto elute ingredients having intended effects at room temperatureefficiently. The components having the flavor-improving effect of theinvention exist in a fraction eluted with the aforementioned solvent.The eluting speed varies depending upon size of the column, a kind ofthe solvent, a kind of the adsorbent resin, and the like. The elutingspeed is not particularly limited, but is preferred to elute at aneluting speed of from 0.1 to 10 in SV and recover the fraction elutedwithin a 6-fold amount by volume of the resin. Additionally, SV (spacevelocity) is a unit for showing the volume per hour of liquid to bepassed to volume of the resin.

A preferred but unlimited examples of a specific embodiment with respectto the adsorption treatment to and the desorption treatment from thesynthetic resin for obtaining the flavor improving agent of theinvention will be described below. That is, one of the examples comprisethat fruit juice or squeeze is allowed to pass through a column filledwith the aromatic resin or acrylic resin at a column temperature of 5 to50° C. and then water is allowed to pass through the column for washingin the column, followed by eluting ingredients adsorbed on the resin inthe column at a column temperature of 5° C. to 50° C. with a 50/50 to99.5/0.5 (volume/volume) of ethanol-water mixed solvent to recover afraction from the elution-initiating point to the point at which theamount of the eluted liquid reaches to a 6-fold volume amount or less ofthat of the resin. The eluate may be recovered by filtering by such amethod as a press filtration, a suction filtration or a centrifugalfiltration, as needed. Additionally, a filtration aid may be used uponthe filtration. Further, since smell of the fraction itself isunnecessary in many cases in utilizing this fraction as a flavorimproving agent for foods and beverages, the smell is removed by such atechnique as concentration by heating or concentration under reducedpressure. Additionally, in the case where the smell of the fractionitself is not problematical, the removal of the smell may not beconducted.

Of the fractions obtained through such steps, those fractions whereinthe amount of substance ratio between polyphenols and saccharides, thelatter after acid hydrolysis of the fraction, (polyphenol/saccharide;PP/SG) is in the range of from 0.1 to 10, preferably in the range offrom 0.2 to 3 are used as the flavor improving agents of the invention.Of such fractions, those fractions are preferred wherein the amount ofsubstance ratio between polyphenols and saccharides before acidhydrolysis of the fraction (polyphenol/saccharide; hereinafter alsoreferred to as PP/SG) is 1 to 100.

As other process, there is illustrated a process of directly extractingfruit juice or squeeze with a solvent such as alcohol, acetone or ethylacetate. Of these, the extraction with ethanol is preferred. Thisprocess is preferably applied to concentrated fruit juice orconcentrated squeeze. This process will be described specificallyhereinafter. First, a high-concentration ethanol aqueous solution suchas an ethanol aqueous solution of 95% or more is preferably used as theethanol solution to be used for the ethanol extraction. This solution ismixed with concentrated fruit juice or concentrated squeeze and issufficiently stirred. Then, it is allowed to stand, followed byrecovering the supernatant. The supernatant is concentrated underreduced pressure to obtain a concentrate and again thehigh-concentration ethanol aqueous solution is added thereto, followedby sufficient stirring. The resulting solution is allowed to stand at atemperature of 10° C. or lower, preferably a sub-zero temperature, morepreferably −10° C. or lower, followed by recovering the supernatant toobtain a specific fraction of the fruit juice or squeeze. Additionally,this process is illustrated for specifically describing the process ofextracting fruit juice or squeeze with a solvent, and the process ofextracting with a solvent is not limited only to this specificallyillustrated process.

Further, the process for obtaining a specific fraction of the inventionwhich is derived from fruit juice or squeeze is not limited only to theaforementioned two processes, but may be any other process. For example,a process of mixing two or more fractions not satisfying the conditionof the invention with respect to PP/SG, and then adjusting the PP/SGvalue so as to satisfy the condition of the invention. Any process maybe employed, but a fraction wherein a PP/SG value after hydrolysis isoutside the range of from 0.1 to 10 fails to provide the effects of theinvention described above even when used as a flavor improving agent.

The PP/SG value is obtained according to, for example, the followingmethod. That is, a polyphenol amount in terms of chlorogenic acid ismeasured with Folin-Ciocalteu method and, separately, an amount ofsugars (sucrose, fructose and glucose) is measured or an amount ofsugars (sucrose, fructose, and glucose) after acid hydrolysis under thehydrolysis condition described below (1% addition of 35% hydrochloricacid, 100° C. and 7 hours) is measured according to the method formeasuring an amount of sugars described below. The PP/SG value iscalculated as molar ratio from the thus obtained amounts of the twosubstances.

Folin-Ciocalteu Method:

100 μL of a sample aqueous solution (the concentration being adjusted toabout 2 mg/ml), 7.5 ml of water, and 300 of a 2-fold diluted aqueoussolution of a phenol reagent (acidity: 1.8N) are added to a test tubeand, after stirring, 1 ml of a 20% sodium carbonate aqueous solution and1.1 ml of water are added thereto, followed by stirring. After thesample is allowed to stand for 1 hour at room temperature, thepolyphenol amount of the sample in terms of chlorogenic acid iscalculated from the absorbance at 765 nm based on a calibration curvewhich is prepared using chlorogenic acid.

Method of Measuring Sucroses:

A high-performance liquid chromatographic method (HPLC method) isemployed.

Column: Shodex Asahipak NH₂ P-50 4E (4.6×250 mm; manufactured by ShowaDenko K.K.)

Mobile phase: MeCN, H₂O

75-430% MeCN (0→460 min, Gradient), 30% MeCN (60-70 min, Isocratic)

Flow rate: 1 ml/min

Detector used: Evaporative light scattering detector (manufactured byAgilent)

Acid Hydrolysis Conditions:

A 5 mg/ml sample aqueous solution is prepared. After 50 μl of conc.(35%) hydrochloric acid is added to 5 ml of the prepared samplesolution, the resulting mixture is refluxed in a 100° C. oil bath. After7 hours are elapsed, the solution is cooled with ice and then 100 μl ofaqueous ammonia (28%) is added thereto to discontinue the reaction.Thus, an acid-hydrolyzed sample is prepared.

The thus-obtained fraction derived from the fruit juice or squeeze with0.1 to 10 in PP/SG after acid hydrolysis, more preferably the fractionwhose PP/SG before acid hydrolysis is 1 to 100, can be used as it is asa flavor improving agent but, usually, after diluting it 2 to 500 timeswith distilled water, an ethanol aqueous solution or the like, thediluted fraction is used as a flavor improving agent.

The term “improvement of flavor” as used in the invention includesenhancement of favorable tastes such as giving a fruit-like feel andgiving a richness as well as reduction of bitterness, astringency,sourness, and harsh taste and improvement of composite flavor of tasteand smell with respect to various products including foods andbeverages, pharmaceutical products, and oral care products.

As foods and beverages whose flavor can be improved with the flavorimproving agent of the invention, there are illustrated foods andbeverages such as health foods and beverages, foods and beveragescontaining fruit flavors, soups, and processed vegetable foods andbeverages, but the foods and beverages of the invention are not limitedonly to these products. Of the above-described foods and beverages,health foods and beverages, foods and beverages containing fruitflavors, and processed vegetable foods and beverages are preferred.

The addition amount of the flavor improving agent of the invention andthe method of adding the flavor improving agent can be properly selectedaccording to kinds of foods and beverages to which the flavor improvingagent is added. The addition amount is usually from 0.1 to 50,000 ppm,preferably 0.5 to 10,000 ppm for foods and beverages. The flavorimproving agent of the invention can give sufficient flavor improvingeffects to foods and beverages when added in an amount within theabove-described range. In case where the addition amount is less thanthe aforementioned range, the intended flavor improving effects mightnot be obtained in some cases. Also, in case where the addition amountis more than the aforementioned range, further improvement of theeffects by the addition might not be obtained or inherent tastes of thefoods and beverages might be spoiled in some cases.

As a method of adding the flavor improving agent of the invention, amethod of mixing the flavor improving agent with foods and beverageswhose flavor is required to be improved is usually employed. Withprocessed foods, it is desirable to directly mix the flavor improvingagent with a raw material whose flavor is required to be improved but,in the case where mixing with the raw material is difficult, it ispossible to spray a solution of the flavor improving agent over thesurface of the raw material whose flavor is required to be improved, orto dip the raw material in such solution, or to bring the raw materialinto contact with a powdery or sheet-like food containing the flavorimproving agent.

Unlimited flavor improvements of foods and beverages with the flavorimproving agent of the invention are illustrated below.

Improvement of Flavor of Health Foods and Beverages (Reduction ofBitterness, Astringency or Sourness)

Health foods and beverages include, for example, health foods and healthbeverages containing polyphenols, organic acids or other naturalingredients. In many cases, such health foods and beverages haveunacceptable peculiar flavor. For example, foods and beveragescontaining polyphenols at a high concentration give bitterness andastringency. Foods and beverages containing an organic acid such ascitric acid, lactic acid, acetic acid or ascorbic acid give a strongsourness. Bitterness, astringency, sourness and the like which thesehealth foods and beverages have can be reduced by adding the flavorimproving agent of the invention to such foods and beverages.

Improvement of Flavor of Foods and Beverages Containing Fruit Flavor(Giving a Fruit-Like Feel)

As the foods and beverages containing fruit flavor, there areillustrated fruit juice beverages, fruit juice-free beverages,carbonated beverages, sports beverages, lactic acid bacterium beverages,flavored tea, candy, gum, yogurt, gummy, jelly, chocolate, ice cream,and the like. Foods and beverages with a better taste to which afruit-like feel is given can be provided by adding the flavor improvingagent of the invention to such foods and beverages. Even when a flavorimproving agent used was prepared from different fruit juice from theflavor of foods or beverages to which the flavor improving agent areadded, a fruit-like feel can be given to the foods or beverages byadding the flavor improving agent of the invention.

Improvement of Flavor of Soups (Giving a Richness)

As soups, there are illustrated Western style soup, Japanese style soup,Chinese style soup, instant-noodle soup, ethnic soup, and the like. Arichness can be given to the tastes of these soups by adding the flavorimproving agent of the invention, thus more delicious soups being ableto be provided.

Improvement of Flavor of Processed Vegetable Foods and Beverages(Reduction of Harsh Taste)

As processed vegetable foods and beverages, there can be illustratedbeverages such as tomato juice, carrot juice, aojiru (green juice), andvegetable juice and processed foods such as jellies containing these. Aharsh taste peculiar to vegetables can be reduced by adding the flavorimproving agent of the invention to these processed vegetable foods andbeverages.

The flavor improving agent of the invention may be mixed with variouscompounds or various known flavor raw materials to prepare flavorcompositions. Since improvement of flavor is made on foods and beveragesor other oral compositions, the flavor composition is particularlypreferably a preparation flavor composition for foods and beverages.

Various compounds capable of being mixed with a flavor composition arenot particularly limited as long as the effects of the flavor improvingagent of the invention are not completely spoiled. As the compounds,there may be used additives commonly used for foods and beverages,pharmaceutical products and oral care products. Specifically, there canbe illustrated sweeteners, acidulants, extenders, antioxidants,colorants, known antiseptics and antibacterial agents, emulsifiers,functional substances, existing flavor improving agents, pH-adjustingagents, milk components, nitrogen-containing compounds such as aminoacids and peptides, and the like. These compounds may be compoundedindependently or in combination of two or more thereof. The compoundingamount of the above-described compounds is not particularly limited aslong as the objects of the invention can be attained.

Examples of the sweeteners described above include sugar, fructose,lactose, glucose, palatinose, maltose, trehalose, sorbitol, erythritol,maltitol, reduced palatinose, xylitol, lactitol, glutinous starch syrup,oligosaccharides, aspartame, sucralose, acesulfam K, saccharin, stevia,neotame, alitame, thaumatin, neohesperidin dihydrochalcone, licorice,and the like.

As the acidulants, there can be illustrated acetic acid, lactic acid,citric acid, and the like. As the extenders, there can be illustratedsugars, polysaccharides, processed starches, casein, gelatin,carboxymethyl cellulose, lecithin, and the like.

As the antioxidants, there are known pyrrolopyrrole derivatives, freeradical scavengers obtained from extracts of various plants, enzymeshaving antioxidant properties such as superoxide dismutase andglutathione peroxidase, and the like as well as butylhydroxytoluene,butylhydroxyanisole, citric acid, bioflavo acid, glutathione, selenium,lycopene, vitamin A, vitamin E, vitamin C, etc., and these can beillustrated as the antioxidants.

As colorants, there are known natural colorants and organic syntheticcolorants which are not hazardous to humans. Specific examples of thecolorants include hibiscus colorant, huckleberry colorant, plumcolorant, seaweed colorant, dewberry colorant, grape juice colorant,blackberry colorant, blueberry colorant, mulberry colorant, morellocherry colorant, red currant colorant, loganberry colorant, paprikapowder, malt extract, rutin, flavonoids, red cabbage colorant, redradish colorant, adzuki bean colorant, turmeric colorant, olive tea,cowberry colorant, chlorella powder, saffron colorant, labiate colorant,strawberry colorant, chiocory colorant, pecan nut colorant, monascuscolorant, safflower colorant, purple sweet potato colorant, laccolorant, spirlina colorant, onion colorant, tamarind colorant, redpepper colorant, Cape jasmine colorant, caramel colorant, lithospermumroot colorant, rosewood colorant, krill colorant, orange colorant,carrot carotin, and the like.

As the known antiseptics and antibacterial agents, there can beillustrated benzoic acid, sodium benzoate, isopropyl p-hydroxybenzoate,isobutyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, methylp-hydroxybenzoate, butyl p-hydroxybenzoate, propyl p-hydroxybenzoate,sodium sulfite, sodium hyposulfite, potassium pyrosulfite, sorbic acid,potassium sorbate, sodium dehydroacetate, thujaplicin, udo extract,Japanese snowbell extract, Artemisia capillaris extract, oolong teaextract, soft roe protein extract, enzyme-decomposed Coix lacryma-jobiL. var. ma-yuen extract, tea catechins, apple polyphenols,pectin-decomposed substance, chitosan, lysozyme, ε-polylysine, and thelike.

As the emulsifiers, various emulsifiers having been conventionally usedfor foods and beverages can be used. Examples thereof include fatty acidmonoglycerides, fatty acid diglycerides, fatty acid triglycerides,propylene glycol fatty acid esters, sugar fatty acid esters,polyglycerin fatty acid esters, lecithin, enzyme-processed lecithin,starch, processed starch, dextrin, sorbitan fatty acid esters, quillajaextract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum,pectin, alginic acid and salts thereof, carrageenan, gelatin, andcasein.

The “functional substance” means a substance having a nutritiousfunction or a living body adjusting function. As the functionalsubstance, there are illustrated animal and plant fats and oils such asdocosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), DHA- and/orEPA-containing fish oil, linoleic acid, γ-linolenic acid, α-linolenicacid, lecithin, diacylglycerol and the like, and derivatives thereof;animal and plant extracts such as rosemary, sage, perilla oil, chitin,chitosan, royal jelly, propolis and the like; vitamins, coenzymes andderivatives thereof such as vitamin A, vitamin D, vitamin E, vitamin F,vitamin K, coenzyme Q10, α-lipoic acid and the like; polyphenols such asγ-oryzanol, catechin, anthocyanin, isoflavone, rutin, chlorogenic acid,theaflavin and the like; vegetable fibers such as hard-to-digest dextrinand the like; sugars such as palatinose, xylitol, oligosaccharide andthe like; salts such as calcium citrate malate and the like;lactoprotein-derived substances such as casein phosphopeptide,lactoferrin, lactic peptide and the like; lactic bacteria;γ-aminobutyric acid; heme iron and the like.

The “pH-adjusting agent” means a substance or formulation usable forkeeping the pH value of the food within an appropriate range. As thepH-adjusting agent, there are illustrated, for example, adipic acid,citric acid, trisodium citrate, glucono-δ-lactone, gluconic acid,potassium gluconate, sodium gluconate, succinic acid, monosodiumsuccinate, disodium succinate, sodium acetate, DL-tartaric acid,L-tartaric acid, DL-potassium hydrogen tartrate, L-potassium hydrogentartrate, DL-sodium tartrate, L-sodium tartrate, potassium carbonate(anhydrous), sodium hydrogen carbonate, sodium carbonate, carbondioxide, lactic acid, sodium lactate, glacial acetic acid, disodiumdihydrogen pyrophosphate, fumaric acid, monosodium fumarate, DL-malicacid, DL-sodium malate, phosphoric acid, dipotassium hydrogen phosphate,potassium dihydrogen phosphate, disodium hydrogen phosphate, sodiumdihydrogen phosphate, and other acidulants.

As the milk component, there are illustrated raw milk; milk; milkpowder; skimmed milk powder; fresh cream, etc.; lactoprotein such ascasein, whey and the like; substances derived from, for example, goatmilk or sheep milk; and substances obtained by decomposing thesematerials or substances.

A known flavor improving agent such as sucralose, cyclodextrin,theanine, hesperidin glycoside, sugar cane extract or the like may beallowed to coexist with the flavor improving agent of the invention.

As the various flavor raw materials, there can be used, for example,natural aromas such as natural essential oils and various syntheticaromas. These aromas are not particularly limited as long as materialsbeing able to use for foods and beverages, pharmaceutical products, andoral care products. As preferred aromas, there are illustrated, forexample, synthetic aromas such as esters, alcohols, aldehydes, ketones,acetals, phenols, ethers, lactones, furans, hydrocarbons, and acids;natural aromas such as plant essential oils, e.g., essential oils ofcitrus fruits such as orange, lemon, lime, and grapefruit, essentialoils prepared from flowers, peppermints, spearmints and spice oils, oilyextracts such as kola nut extract, coffee extract, vanilla extract,cocoa extract, black tea extract, green tea extract, oolong tea extractand extracts of spices, and oleoresins, essences and recovered aromasthereof, etc.; and mixtures of plural aromas and essential oils selectedfrom these materials. Further, there can also be used aromas describedin, for example, “Investigation on the Actual Using State of Food FlavorCompounds in Japan” (Welfare Science Research Report, 2000; published inMarch 2001 by Japan Flavor and Fragrance Material Association), Gen-ichiIndo “Synthesized Flavor and Fragrances, Chemistry and MerchandiseInformation” (published on Mar. 6, 1996 by Chemical Daily Co., Ltd.),and Steffen Arctender “Perfume and Flavor Chemicals (Aroma Chemicals) 1,2” (1969).

The compounding amount of the flavor improving agent is preferably from0.001 to 50% based on the weight of the entire prepared flavorcomposition. The addition amount of the flavor composition to variousproducts is preferably from 0.01 to 10%.

Further, the flavor improving agent of the invention can be added to apharmaceutical product such as a liquid internal medicine to improve thetaste of the medicine upon its uptake, thus providing a palatablepharmaceutical product. The compounding amount in this case may be inany range as long as the effect of improving the flavor can be obtainedwithout inhibiting the medicinal effect of the pharmaceutical product.The amount thereof may be the same as the addition amount for ordinaryfoods and beverages.

Furthermore, the flavor improving agent of the invention may be added tooral care products. As the oral care products, there are illustrated,for example, toothpastes, mouth-cleaning products, mouthwashes, and thelike. The addition amount in this case is also the same as the additionamount for foods and beverages.

EXAMPLES

The present invention will be described by reference to Examples.However, the invention is not limited only to such Examples.Additionally, in Examples, “%” means “% by weight” unless otherwisespecified.

Example 1 Preparation of Flavor Improving Agent Derived from PineappleJuice

800 g of water was added to 414 g of pineapple concentrated cloudy juice(Bx. 55; manufactured by Sanyo Foods Co., Ltd.) to dilute. The dilutedfruit juice was mixed with 50 g of Celite 545 (“Celite” being aregistered trademark; sold by Nacalai tesque), followed by suctionfiltration to obtain 1,055 g of a diluted fruit juice (Bx. 18.8) fromwhich fibrous substances were removed. This juice was allowed to pass ata flow rate of SV=6 through a column (column size: inner diameter: 5 cm;height: 13.5 cm) filled with 180 g of AMBERLITE XAD-1180 (manufacturedby Organo Corporation). After completion of the pass-through operation,1,540 g of water was allowed to pass at SV=6 for washing. Next, 439 g ofa 74% ethanol aqueous solution was allowed to pass at SV=2 to therebyelute adsorbed ingredients. 430 g of the thus-obtained eluate was mixedwith 43 g of Celite 545 and, after suction filtration, the filtrate wasdiluted with ethanol and water to obtain 515 g of a sample of flavorimproving agent derived from pineapple juice (solid content: 0.4%).

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured according to theaforementioned Folin-Ciocalteu method and, as a result, the polyphenolamount of the raw fruit juice was found to be 0.445 mmol, and that ofthe sample to be 0.174 mmol. Then, sugar amounts were measured accordingto the aforementioned predetermined method, and the sugar amount of theraw fruit juice was found to be 79.0 mmol, and that of the sample to be0.0172 mmol. From these results, the raw fruit juice was found to havePP/SG before hydrolysis of 0.00563, and the sample was found to havePP/SG before hydrolysis of 10.1. Further, as a result of measuring thesugar amount in the same manner after acid hydrolysis according to theaforementioned predetermined method, the amount of sugar of the rawmaterial was found to be 79.4 mmol and that of the sample was found tobe 0.138 mmol. From these results, the raw fruit juice was found to havePP/SG after hydrolysis of 0.00560 and the sample was found to have PP/SGafter hydrolysis of 1.26.

Comparative Example 1 Preparation of Comparative Sample Fraction ADerived from Pineapple Juice

800 g of water was added to 414 g of pineapple concentrated cloudy juice(Bx. 55; manufactured by Sanyo Foods Co., Ltd.) to dilute. The dilutedfruit juice was mixed with 50 g of Celite 545, followed by suctionfiltration to obtain 1,055 g of a diluted fruit juice (Bx. 18.8) fromwhich fibrous substances were removed. This juice was allowed to pass ata flow rate of SV=6 through a column (column size: inner diameter: 5 cm;height: 13.5 cm) filled with 180 g of AMBERLITE XAD-1180. Aftercompletion of the pass-through operation, 1,540 g of water was allowedto pass at SV-6 for washing. Subsequently, 439 g of a 74% ethanolaqueous solution was allowed to pass at SV=2 to recover an eluate. 430 gof the thus-obtained eluate was mixed with 43 g of Celite 545 andsuction-filtered to obtain 410 g of a sample (solid content: 0.5%).After the solvent was removed by distillation using an evaporator, 15 gof ethyl acetate was added thereto to prepare a suspension. Thissuspension was loaded on a column (column size: inner diameter: 5 cm;height: 22 cm) filled with an ethyl acetate slurry of 200 g of silicagel BW-820 MH (manufactured by Fuji Silysia Chemical Ltd.) for columnchromatography, and eluted with 426 ml of ethyl acetate. Ethyl acetatewas removed from the recovered eluate and the eluate was diluted withethanol to obtain 100 g of a 50% ethanol solution.

The polyphenol amount in terms of chlorogenic acid in 50 g of theobtained sample was measured according to the aforementionedFolin-Ciocalteu method and, as a result, the polyphenol amount of thesample was found to be 0.0445 mmol. Then, sugar amounts were measuredbefore and after acid hydrolysis according to the aforementionedpredetermined method. The sugar amount of the sample before hydrolysiswas found to be 0.00205 mmol and that of the sample after hydrolysis wasfound to be 0.00231 mmol. From these results, the sample was found tohave PP/SG before hydrolysis of 21.7 and PP/SG after hydrolysis of 19.3.

Comparative Example 2 Preparation of Comparative Sample Fraction BDerived from Pineapple Juice

800 g of water was added to 414 g of pineapple concentrated cloudy juice(Bx. 55; manufactured by Sanyo Foods Co., Ltd.) to dilute. The dilutedfruit juice was mixed with 50 g of Celite 545, followed by suctionfiltration to obtain 1,055 g of a diluted fruit juice (Bx. 18.8) fromwhich fibrous substances were removed. This juice was allowed to pass ata flow rate of SV-6 through a column (column size: inner diameter: 5 cm;height: 13.5 cm) filled with 180 g of AMBERLITE XAD-1180 and thepass-through solution was recovered. Subsequently, 1,540 g of water wasallowed to pass through the column at SV=6 to recover the pass-throughsolution. Further, 439 g of a 74% ethanol aqueous solution was allowedto pass through the column at SV=2 to recover an eluate. All of therecovered solutions were combined, mixed with 60 g of Celite 545, andsuction-filtered to obtain 2,900 g of a resin-treated sample (solidcontent: 7.8%).

The polyphenol amount in terms of chlorogenic acid in 50 g of theobtained sample was measured according to the aforementionedFolin-Ciocalteu method and, as a result, the polyphenol amount of thesample was found to be 0.0619 mmol. Then, sugar amounts were measuredbefore and after acid hydrolysis according to the aforementionedpredetermined method. The sugar amount of the sample before hydrolysiswas found to be 10.9 mmol and that of the sample after hydrolysis wasfound to be 10.9 mmol. From these results, the sample was found to havePP/SG before hydrolysis of 0.00567 and PP/SG after hydrolysis of0.00567.

Examples 2 and 3, and Comparative Examples 3 to 6 Suppression ofSourness of Diluted Black Vinegar

Commercially available drinking vinegar “Jun Genmai Kurozu” (pure blackvinegar of unpolished rice) (manufactured by Mizkan Co., Ltd.) wasdiluted with 4-fold amount of water, and the sample obtained in Example1 which was derived from pineapple juice was added thereto to aconcentration of 100 ppm to prepare a sample solution of Example 2 oradded thereto to a concentration of 10,000 ppm to prepare a samplesolution of Example 3. Also, for comparison, there were prepared asample solution of Comparative Example 3 by adding the raw pineappleconcentrated cloudy juice to Jun Genmai Kurozu to a concentration of9,100 ppm, a sample solution of Comparative Example 4 by adding a 1%hesperidin mixture solution (hesperidin (manufactured by TCI): αGhesperidin (manufactured by Toyo Sugar Refining Co., Ltd.) =3:7) to JunGenmai Kurozu to a concentration of 10,000 ppm, a sample solution ofComparative Example 5 by adding the comparative sample A obtained inComparative Example 1 which was derived from pineapple juice to JunGenmai Kurozu to a concentration of 1,950 ppm, and a sample solution ofComparative Example 6 by adding the comparative sample fraction Bobtained in Comparative Example 2 which was derived from pineapple juiceto Jun Genmai Kurozu to a concentration of 57,000 ppm. Additionally, theaddition amounts of the comparative sample fractions A and B weredetermined as amounts corresponding to the addition amount of the samplesolution of Example 3.

For examining difference between the sample solutions of Examples 2 and3 and the comparative sample solutions by sensory evaluation, 6panelists were asked to compare these by drinking. As a result, with thesample solution to which pineapple juice was added, 2 out of 6 panelistsevaluated as “weak sourness-suppressing effect being recognized” and 4panelists evaluated as “no effects being recognized”. With the samplesolution to which the hesperidin mixture solution was added, 3 out of 6panelists evaluated as “weak sourness-suppressing effect beingrecognized” and 3 evaluated as “no effects being recognized”. With thesample solution to which the comparative sample A derived from pineapplejuice was added to a concentration of 1,950 ppm, 3 out of 6 panelistsevaluated as “weak sourness-suppressing effect being recognized” and 3evaluated as “no effects being recognized”. With the sample solution towhich the comparative sample fraction B was added, 2 out of 6 panelistsevaluated as “weak sourness-suppressing effect being recognized” and 4panelists evaluated as “no effects being recognized”. In contrast, withthe sample solution to which the sample of Example 1 derived frompineapple juice was added to a concentration of 100 ppm, 3 out of 6panelists evaluated as “strong sourness-suppressing effect beingrecognized” and 3 panelists evaluated as “weak sourness-suppressingeffect being recognized”. Further, with the sample solution to which thesample of Example 1 derived from pineapple juice was added to aconcentration of 10,000 ppm, 5 out of 6 panelists evaluated as “strongsourness-suppressing effect being recognized” and 1 panelist evaluatedas “weak sourness-suppressing effect being recognized”. Thus, nopanelists evaluated the two sample solutions of Examples 2 and 3 as “noeffects being recognized”. Results of these are shown in Table 1.

TABLE 1 Suppression effect of sourness Flavor improving agent StrongWeak No effects Example 2 Fraction derived from 3 3 0 pineapple juice:100 ppm Example 3 Fraction derived from 5 1 0 pineapple juice: 10,000ppm Comparative Pineapple juice 0 2 4 Example 3 Comparative Hesperidinmixture 0 3 3 Example 4 Comparative Comparative fraction A 0 3 3 Example5 derived from pineapple juice Comparative Comparative fraction B 0 2 4Example 6 derived from pineapple juice

From the above-described results, it has become apparent that thefraction of Example 1 derived from pineapple juice has the effect ofreducing sourness of black vinegar. It is also seen that, even if thefraction is a fraction derived from pineapple juice, there is obtainedonly weak or almost no effect of improving the flavor in the case wherethe obtained fraction has PP/SG after acid hydrolysis outside the rangeof from 0.1 to 10.

Example 4 and Comparative Examples 7 and 8 Suppression of Sourness ofApple Vinegar

Commercially available drinking vinegar “Ringo Su” (apple vinegar)(manufactured by Mizkan Co., Ltd.) was diluted with 5.25-fold amount ofwater, and the sample obtained in Example 1 which was derived frompineapple juice was added thereto to a concentration of 10,000 ppm toprepare a sample solution of Example 4. Further, for comparison, therewere prepared a sample solution of Comparative Example 7 by adding theraw pineapple concentrated cloudy juice to the diluted Ringo Su to aconcentration of 9,100 ppm and a sample solution of Comparative Example8 by adding a 1% hesperidin mixture solution (hesperidin (manufacturedby TCI): αG hesperidin (manufactured by Toyo Sugar Refining Co., Ltd.)=3:7) to the diluted Ringo Su to a concentration of 10,000 ppm.

For examining difference between the sample solution of Example 4 andthe comparative sample solutions by sensory evaluation, 11 panelistswere asked to compare these by drinking. As a result, with the samplesolution to which pineapple juice was added, 2 out of 11 panelistsevaluated as “weak sourness-suppressing effect being recognized” and 9panelists evaluated as “no effects being recognized”. With the samplesolution to which the hesperidin mixture solution was added, 5 out of 11panelists evaluated as “weak sourness-suppressing effect beingrecognized”, and 6 evaluated as “no effects being recognized”. On theother hand, with the sample solution of Example 4, 8 out of 11 panelistsevaluated as “strong sourness-suppressing effect being recognized”, and3 panelists evaluated as “weak sourness-suppressing effect beingrecognized”, thus no panelists evaluating the sample solution of Example4 as “no effects being recognized”. Results are shown in Table 2.

TABLE 2 Flavor improving Suppression effect of sourness agent StrongWeak No effects Example 4 Fraction derived 8 3 0 from pineapple juiceComparative Pineapple juice 0 2 9 Example 7 Comparative Hesperidinmixture 0 5 6 Example 8

From the above-described results, it has become apparent that thefraction of Example 1 derived from pineapple juice has the effect ofreducing sourness of apple vinegar.

Example 5 and Comparative Examples 9 and 10 Effect of SuppressingBitterness and Astringency of Catechin

The sample obtained in Example 1 which was derived from pineapple juicewas added to a commercially available drinking beverage “Healthya Water”(manufactured by Kao Corporation) rich in catechin (540 mg/500 ml) to aconcentration of 1,000 ppm to prepare a sample solution of Example 5.Further, for comparison, there were prepared a sample solution ofComparative Example 9 by adding the raw pineapple concentrated cloudyjuice to Healthya Water to a concentration of 910 ppm and a samplesolution of Comparative Example by adding a 1% hesperidin mixturesolution (hesperidin (manufactured by TCI): αG hesperidin (manufacturedby Toyo Sugar Refining Co., Ltd.)-3:7) to Healthya Water to aconcentration of 1,000 ppm.

For examining difference between the sample solution of Example 5 andthe comparative sample solutions by sensory evaluation, 6 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which pineapple juice was added, 2 out of 6 panelistsevaluated as “weak bitterness- and astringency-suppressing effects beingrecognized” and 4 panelists evaluated as “no effects being recognized”.With the sample solution to which the hesperidin mixture solution wasadded, 1 out of 6 panelists evaluated as “weak bitterness- andastringency-suppressing effects being recognized” and 5 evaluated as “noeffects being recognized”. On the other hand, with the sample solutionof Example 5, 5 out of 6 panelists evaluated as “strong bitterness- andastringency-suppressing effects being recognized” and 1 panelistevaluated as “weak bitterness- and astringency-suppressing effects beingrecognized”, thus no panelists evaluating the sample solution of Example5 as “no effects being recognized”. Results are shown in Table 3.

TABLE 3 Suppression effect of bitterness Flavor improving andastringency agent Strong Weak No effects Example 5 Fraction derived 5 10 from pineapple juice Comparative Pineapple juice 0 2 4 Example 9Comparative Hesperidin mixture 0 1 5 Example 10

From the above-described results, it has become apparent that thefraction of Example 1 derived from pineapple juice has the effect ofreducing bitterness and astringency of high-content catechin.

Example 6 Preparation of Flavor Improving Agent Derived from Grape Juice

216 g of 95 v/v % ethanol was added to 144 g of concentrated grape juice(Bx. 68; manufactured by TECNOVIN DO BRAZIL IND.) and after sufficientlymixing, the mixture was allowed to stand at room temperature for 2hours. After the mixture was allowed to stand, the supernatant wasrecovered to obtain 240 g of a solution. This solution was concentratedunder reduced pressure to obtain 60 g of a concentrated liquid. 60 g of95 v/v % ethanol was added to this concentrated liquid and, aftersufficiently stirring, the mixture was allowed to stand at −20° C. for18 hours. After the mixture was allowed to stand, the supernatant wasrecovered and 75 g of the thus-obtained solution (solid content: 12.0%)was referred to as a sample of flavor improving agent derived from grapejuice. This sample did not have grape-like aroma.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured. As a result, thepolyphenol amount of the raw fruit juice was found to be 3.22 mmol andthat of the sample to be 3.82 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 137 mmol and that of the sampleto be 3.12 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.0235 and the sample was found to havePP/SG before hydrolysis of 1.22. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 156 mmol and that of thesample was found to be 25.6 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.0206 and the samplewas found to have PP/SG after hydrolysis of 0.149.

Example 7 and Comparative Examples 11 and 12 Effect of Suppressing HarshTaste of Vegetables

The sample obtained in Example 6 which was derived from grape juice wasadded to commercially available green juice “Super Aojiru” (manufacturedby Fancl Corporation) to a concentration of 10,000 ppm to prepare asample solution of Example 7. Further, for comparison, there wereprepared a sample solution of Comparative Example 11 by adding the rawgrape concentrated juice to Super Aojiru to a concentration of 19,800ppm and a sample solution of Comparative Example 12 by adding a 1%hesperidin mixture solution (hesperidin (manufactured by TCI): αcGhesperidin (manufactured by Toyo Sugar Refining Co., Ltd.) =3:7) toSuper Aojiru to a concentration of 25,000 ppm.

For examining difference between the sample solution of Example 7 andthe comparative sample solutions by sensory evaluation, 8 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which grape juice was added, 3 out of 8 panelists evaluatedas “weak harsh taste-suppressing effect being recognized” and 5panelists evaluated as “no effects being recognized”. With the samplesolution to which the hesperidin mixture solution was added, 3 out of 8panelists evaluated as “weak harsh taste-suppressing effect beingrecognized” and 5 evaluated as “no effects being recognized”. On theother hand, with the sample solution of Example 7, 6 out of 8 panelistsevaluated as “strong harsh taste-suppressing effect being recognized”and 2 panelists evaluated as “weak harsh taste-suppressing effect beingrecognized”, thus no panelists evaluating the sample solution of Example7 as “no effects being recognized”. Results are shown in Table 4.

TABLE 4 Flavor improving Suppression effect of harsh taste agent StrongWeak No effects Example 7 Fraction derived 6 2 0 from grape juiceComparative Grape juice 0 3 5 Example 11 Comparative Hesperidin mixture0 3 5 Example 12

From the above-described results, it has become apparent that thefraction of Example 6 derived from grape juice has the effect ofreducing harsh taste of vegetables.

Example 8 Preparation of Flavor Improving Agent Derived from Peach Juice

257 g of water was added to 245 g of concentrated peach juice (Bx. 40.5;manufactured by Sanyo Foods Co., Ltd.) to dilute. The water-dilutedpeach juice obtained had Bx. 19.8. The diluted fruit juice was allowedto pass at a flow rate of SV=5 through a column (column size: innerdiameter: 5 cm; height: 11 cm) filled with 150 g of AMBERLITE XAD-1180(manufactured by Organo Corporation). After completion of thepass-through operation, 1,300 g of water was allowed to pass at SV=5 forwashing. Next, 370 g of a 74% ethanol aqueous solution was allowed topass at SV=2.5 to thereby elute adsorbed ingredients. 379 g of thethus-obtained eluate was mixed with 4 g of Celite 545 and, after suctionfiltration, there was obtained 366 g of a filtrate (solid content:0.25%) which was referred to as a sample of flavor improving agentderived from peach juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.145 mmol andthat of the sample to be 0.0349 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 70.4 mmol and that of the sampleto be 0.00914 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.0206 and the sample was found to havePP/SG before hydrolysis of 3.82. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 70.8 mmol and that of thesample was found to be 0.107 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00205 and the samplewas found to have PP/SG after hydrolysis of 0.326.

Example 9 and Comparative Example 13 Effect of Giving a Richness

A soup was prepared from commercially available powdered corn soup“Knorr Cup Soup Corn Cream” (manufactured by Ajinomoto Co., Inc.)(“Knorr” is a registered trade mark.) according to the instruction. Thesample obtained in Example 8 which was derived from peach juice wasadded to the soup to a concentration of 40,000 ppm to prepare a samplesolution of Example 9. Further, for comparison, a sample solution ofComparative Example 13 was prepared by adding the raw peach juice to thesoup to a concentration of 25,000 ppm.

For examining difference between the sample solution of Example 9 andthe comparative sample solutions by sensory evaluation, 10 panelistswere asked to compare these by drinking. As a result, with the samplesolution to which peach juice was added, 1 out of 10 panelists evaluatedas “weak effect of giving a richness being recognized” and 9 panelistsevaluated as “no effects being recognized”. On the other hand, with thesample solution of Example 9, 7 out of 10 panelists evaluated as “strongeffect of giving a richness being recognized” and 3 panelists evaluatedas “weak effect of giving a richness being recognized”, thus nopanelists evaluating the sample solution of Example 9 as “no effectsbeing recognized”. Results are shown in Table 5.

TABLE 5 Flavor improving Effect of giving a richness agent Strong WeakNo effects Example 9 Fraction derived 7 3 0 from peach juice ComparativePeach juice 0 1 9 Example 13

From the above-described results, it has become apparent that thefraction of Example 8 derived from peach juice has the effect of givinga richness.

Example 10 Preparation of Flavor Improving Agent Derived from AppleJuice

311 g of water was added to 189 g of concentrated apple juice (Bx. 53;manufactured by Aomori Ringo Kako K.K.) to dilute. The water-dilutedapple juice obtained had Bx. 20.2. The diluted fruit juice was allowedto pass at a flow rate of SV=5 through a column (column size: innerdiameter: 5 cm; height: 5 cm) filled with 70 g of AMBERLITE XAD-2(manufactured by Organo Corporation). After completion of thepass-through operation, 500 g of water was allowed to pass at SV=5 forwashing. Next, 170 g of a 74% ethanol aqueous solution was allowed topass through the column at SV=3 to thereby elute adsorbed ingredients.175 g of the thus-obtained eluate was heated to 60° C. and concentratedunder reduced pressure to obtain 0.33 g of a solid product. 33 g of a74% ethanol aqueous solution was added thereto to dissolve the solidproduct, followed by suction filtration to obtain 28 g of a filtrate(solid content: 1.0%) which was referred to as a sample of flavorimproving agent derived from apple juice. This sample did not have anapple-like aroma.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.396 mmol andthat of the sample to be 1.04 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method, and the sugaramount of the raw fruit juice was found to be 119 mmol and that of thesample to be 0.0268 mmol. From these results, the raw fruit juice wasfound to have PP/SG before hydrolysis of 0.00333 and the sample wasfound to have PP/SG before hydrolysis of 38.8. Also, as a result ofmeasuring the sugar amount in the same manner after acid hydrolysis, theamount of sugar of the raw material was found to be 119 mmol and that ofthe sample was found to be 0.429 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00333 and the samplewas found to have PP/SG after hydrolysis of 2.42.

Example 11 and Comparative Example 14 Effect of Giving a Juice-Like Feel

Water was added to 214 g of high fructose corn syrup and 2.6 g of citricacid to prepare 400 g of an aqueous solution and, further, 1600 g ofcarbonated water and 2 g of a grapefruit flavor were added thereto toprepare a material. The sample obtained in Example 10 which was derivedfrom apple juice was added to this material to a concentration of 2,000ppm to prepare a sample solution of Example 11. Also, for comparison, asample solution of Comparative Example 14 was prepared by adding the rawapple juice to the material to a concentration of 1,400 ppm.

For examining difference between the sample solution of Example 11 andthe comparative sample solution by sensory evaluation, 10 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which apple juice was added, 4 out of 10 panelists evaluatedas “weak effect of giving a juice-like feel being recognized” and 6panelists evaluated as “no effects being recognized”. On the other hand,with the sample solution of Example 11, 8 out of 10 panelists evaluatedas “strong effect of giving a juice-like feel being recognized” and 2panelists evaluated as “weak effect of giving a juice-like feel beingrecognized”, thus no panelists evaluating the sample solution of Example11 as “no effects being recognized”. Results are shown in Table 6.

TABLE 6 Flavor improving Suppression effect of harsh taste agent StrongWeak No effects Example 11 Fraction derived 8 2 0 from apple juiceComparative Apple juice 0 4 6 Example 14

From the above-described results, it has become apparent that thefraction of Example 10 derived from apple juice has the effect of givinga juice-like feel.

Example 12 Preparation of Flavor Improving Agent Derived from StrawberryJuice

155 g of water was added to 356 g of concentrated strawberry juice (Bx.28.3; manufactured by IWATABUSSAN CO., LTD) to dilute. The water-dilutedstrawberry juice obtained had Bx. 19.8. The diluted fruit juice wasallowed to pass at a flow rate of SV=8 through a column (column size:inner diameter: 5 cm; height: 7.5 cm) filled with 100 g of DIAION HP20(manufactured by Mitsubishi Chemical). After completion of thepass-through operation, 890 g of water was allowed to pass through thecolumn at SV=8 for washing. Next, 300 g of a 74% ethanol aqueoussolution was allowed to pass through the column at SV=3 to thereby eluteadsorbed ingredients. 290 g of the thus-obtained eluate was mixed with 3g of Celite 545, followed by suction filtration to obtain 278 g of afiltrate (solid content: 0.29%) which was referred to as a sample offlavor improving agent derived from strawberry juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.289 mmol andthat of the sample to be 0.181 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 45.5 mmol and that of the sampleto be 0.00863 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00635 and the sample was found to havePP/SG before hydrolysis of 21.0. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 45.7 mmol and that of thesample was found to be 0.185 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00632 and the samplewas found to have PP/SG after hydrolysis of 0.978.

Example 13 and Comparative Example 15 Effect of Giving a Juice-Like Feel

Water was added to 214 g of high fructose corn syrup and 2.6 g of citricacid to prepare 400 g of an aqueous solution and, further, 1600 g ofcarbonated water and 2 g of an apple flavor were added thereto toprepare a material. The sample obtained in Example 12 which was derivedfrom strawberry juice was added to the material to a concentration of1,400 ppm to prepare a sample solution of Example 13. Also, forcomparison, a sample solution of Comparative Example 15 was prepared byadding the raw strawberry juice to a concentration of 1,800 ppm.

For examining difference between the sample solution of Example 13 andthe comparative sample solution by sensory evaluation, 10 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which strawberry juice was added, 3 out of 10 panelistsevaluated as “weak effect of giving a juice-like feel being recognized”and 7 panelists evaluated as “no effects being recognized”. On the otherhand, with the sample solution of Example 13, 6 out of 10 panelistsevaluated as “strong effect of giving a juice-like feel beingrecognized” and 4 panelists evaluated as “weak effect of giving ajuice-like feel being recognized”, thus no panelists evaluating thesample solution of Example 13 as “no effects being recognized”. Resultsare shown in Table 7.

TABLE 7 Flavor improving Effect of giving a juice-like feel agent StrongWeak No effects Example 13 Fraction derived 6 4 0 from strawberry juiceComparative Strawberry juice 0 3 7 Example 15

From the above-described results, it has become apparent that thefraction of Example 12 derived from strawberry juice has the effect ofgiving a juice-like feel.

Example 14 Preparation of Flavor Improving Agent Derived from BlueberryJuice

346 g of water was added to 155 g of concentrated blueberry juice (Bx.65.1; manufactured by Eiko Boeki K.K.) to dilute. The water-dilutedblueberry juice obtained had Bx. 20.8. The diluted fruit juice wasallowed to pass at a flow rate of SV=5 through a column (column size:inner diameter: 10.5 cm; height: 8.5 cm) filled with 500 g of DIAIONHP20 (manufactured by Mitsubishi Chemical). After completion of thepass-through operation, 4,500 g of water was allowed to pass through thecolumn at SV=6 for washing. Next, 1,250 g of a 74% ethanol aqueoussolution was allowed to pass through the column at SV=2 to thereby eluteadsorbed ingredients. 1,300 g of the thus-obtained eluate was mixed with15 g of Celite 545, followed by suction filtration to obtain 1,250 g ofa filtrate (solid content: 0.25%) which was referred to as a sample offlavor improving agent derived from blueberry juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 4.52 mmol andthat of the sample to be 0.436 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 119 mmol and that of the sampleto be 0.00846 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.0380 and the sample was found to havePP/SG before hydrolysis of 51.5. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 121 mmol and that of thesample was found to be 0.223 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.0374 and the samplewas found to have PP/SG after hydrolysis of 1.96.

Example 15 and Comparative Example 16 Effect of Giving a Juice-Like Feel

Water was added to 214 g of high fructose corn syrup and 2.6 g of citricacid to prepare 400 g of an aqueous solution and, further, 1,600 g ofcarbonated water and 2 g of a peach flavor were added thereto to preparea material. The sample obtained in Example 14 which was derived fromblueberry juice was added to this material to a concentration of 1,600ppm to prepare a sample solution of Example 15. Further, for comparison,a sample solution of Comparative Example 16 was prepared by adding theraw blueberry juice to a concentration of 230 ppm.

For examining difference between the sample solution of Example 15 andthe comparative sample solution by sensory evaluation, 10 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which blueberry juice was added, 2 out of 10 panelistsevaluated as “weak effect of giving a juice-like feel being recognized”and 8 panelists evaluated as “no effects being recognized”. On the otherhand, with the sample solution of Example 15, 6 out of 10 panelistsevaluated as “strong effect of giving a juice-like feel beingrecognized” and 4 panelists evaluated as “weak effect of giving ajuice-like feel being recognized”, thus no panelists evaluating thesample solution of Example 15 as “no effects being recognized”. Resultsare shown in Table 8.

TABLE 8 Flavor improving Effect of giving a juice-like feel agent StrongWeak No effects Example 15 Fraction derived 6 4 0 from blueberry juiceComparative Blueberry juice 0 2 8 Example 16

From the above-described results, it has become apparent that thefraction of Example 14 derived from blueberry juice has the effect ofgiving a juice-like feel.

Example 16 Preparation of Flavor Improving Agent Derived from MangoJuice

350 g of water was added to 150 g of concentrated mango juice (Bx. 66.1;manufactured by Eiko Boeki K.K.) to dilute. The water-diluted mangojuice obtained had Bx. 20.3. The diluted fruit juice was allowed to passat a flow rate of SV=4 through a column (column size: inner diameter: 5cm; height: 9 cm) filled with 120 g of DIAION HP20 (manufactured byMitsubishi Chemical). After completion of the pass-through operation,1,060 g of water was allowed to pass through the column at SV-6 forwashing. Next, 300 g of a 74% ethanol aqueous solution was allowed topass through the column at SV=1 to thereby elute adsorbed ingredients.250 g of the thus-obtained eluate was mixed with 5 g of Celite 545,followed by suction filtration to obtain 238 g of a filtrate (solidcontent: 0.74%) which was referred to as a sample of flavor improvingagent derived from mango juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.361 mmol andthat of the sample to be 0.0740 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 99.7 mmol and that of the sampleto be 0.0120 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00362 and the sample was found to havePP/SG before hydrolysis of 6.17. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 101 mmol and that of thesample was found to be 0.184 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00357 and the samplewas found to have PP/SG after hydrolysis of 0.402.

Example 17 and Comparative Example 17 Effect of Giving a Juice-Like Feel

Water was added to 214 g of high fructose corn syrup and 2.6 g of citricacid to prepare 400 g of an aqueous solution and, further, 1,600 g ofcarbonated water and 2 g of a banana flavor were added thereto toprepare a material. The sample obtained in Example 16 which was derivedfrom mango juice was added to this material to a concentration of 540ppm to prepare a sample solution of Example 17. Also, for comparison, asample solution of Comparative Example 17 was prepared by adding the rawmango juice to the material to a concentration of 380 ppm.

For examining difference between the sample solution of Example 17 andthe comparative sample solution by sensory evaluation, 10 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which mango juice was added, 3 out of 10 panelists evaluatedas “weak effect of giving a juice-like feel being recognized” and 7panelists evaluated as “no effects being recognized”. On the other hand,with the sample solution of Example 17, 6 out of 10 panelists evaluatedas “strong effect of giving a juice-like feel being recognized” and 4panelists evaluated as “weak effect of giving a juice-like feel beingrecognized”, thus no panelists evaluating the sample solution of Example17 as “no effects being recognized”. Results are shown in Table 9.

TABLE 9 Flavor improving Effect of giving a juice-like feel agent StrongWeak No effects Example 17 Fraction derived 6 4 0 from mango juiceComparative Mango juice 0 3 7 Example 17

From the above-described results, it has become apparent that thefraction of Example 16 derived from mango juice has the effect of givinga juice-like feel.

Example 18 Preparation of Flavor Improving Agent Derived from MelonJuice

196 g of water was added to 304 g of concentrated melon juice (Bx. 32.8;manufactured by IWATABUSSAN CO., LTD.) to dilute. The water-dilutedmelon juice obtained had Bx. 20.1. The diluted fruit juice was allowedto pass at a flow rate of SV=5 through a column (column size: innerdiameter: 5 cm; height: 9 cm) filled with 120 g of DIAION HP20(manufactured by Mitsubishi Chemical). After completion of thepass-through operation, 1,060 g of water was allowed to pass through thecolumn at SV=5 for washing. Next, 300 g of a 74% ethanol aqueoussolution was allowed to pass through the column at SV=2 to thereby eluteadsorbed ingredients. 290 g of the thus-obtained eluate was mixed with 4g of Celite 545, followed by suction filtration to obtain 276 g of afiltrate (solid content: 0.42%) which was referred to as a sample offlavor improving agent derived from melon juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.273 mmol andthat of the sample to be 0.0937 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 43.4 mmol, and that of the sampleto be 0.0243 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00629 and the sample was found to havePP/SG before hydrolysis of 3.86. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 44.3 mmol and that of thesample was found to be 0.347 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00616 and the samplewas found to have PP/SG after hydrolysis of 0.270.

Example 19 and Comparative Example 18 Effect of Giving a Juice-Like Feel

Water was added to 214 g of high fructose corn syrup and 2.6 g of citricacid to prepare 400 g of an aqueous solution and, further, 1,600 g ofcarbonated water and 2 g of an orange flavor were added thereto toprepare a material. The sample obtained in Example 18 which was derivedfrom melon juice was added to this material to a concentration of 950ppm to prepare a sample solution of Example 19. Further, for comparison,a sample solution of Comparative Example 18 was prepared by adding theraw melon juice to the material to a concentration of 1,070 ppm.

For examining difference between the sample solution of Example 19 andthe comparative sample solution by sensory evaluation, 10 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which melon juice was added, 3 out of 10 panelists evaluatedas “weak effect of giving a juice-like feel being recognized” and 7panelists evaluated as “no effects being recognized”. On the other hand,with the sample solution of Example 19, 6 out of 10 panelists evaluatedas “strong effect of giving a juice-like feel being recognized” and 4panelists evaluated as “weak effect of giving a juice-like feel beingrecognized”, thus no panelists evaluating the sample solution of Example19 as “no effects being recognized”. Results are shown in Table 10.

TABLE 10 Flavor improving Effect of giving a juice-like feel agentStrong Weak No effects Example 19 Fraction derived 6 4 0 from melonjuice Comparative Melon juice 0 3 7 Example 18

From the above-described results, it has become apparent that thefraction of Example 18 derived from melon juice has the effect of givinga juice-like feel.

Example 20 Preparation of Flavor Improving Agent Derived from OrangeJuice

350 g of water was added to 300 g of concentrated orange juice (Bx.40.9; manufactured by CIS SICILY) to dilute. The water-diluted orangejuice obtained had Bx. 18.9. The diluted fruit juice was allowed to passat a flow rate of SV=10 through a column (column size: inner diameter: 3cm; height: 12.1 cm) filled with 60 g of AMBERLITE XAD-1180(manufactured by Organo Corporation). After completion of thepass-through operation, 500 g of water was allowed to pass through thecolumn at SV=10 for washing. Next, 140 g of a 92% ethanol aqueoussolution was allowed to pass through the column at SV=4 to thereby eluteadsorbed ingredients. 140 g of the thus-obtained eluate (solid content:0.30%) was referred to as a sample of flavor improving agent derivedfrom orange juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.310 mmol andthat of the sample to be 0.314 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 39.4 mmol and that of the sampleto be 0.0357 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00787 and the sample was found to havePP/SG before hydrolysis of 8.80. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 40.1 mmol and that of thesample was found to be 0.693 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00773, and thesample was found to have PP/SG after hydrolysis of 0.453.

Example 21 and Comparative Examples 19 and 20 Effect of SuppressingSourness of Apple Vinegar

Commercially available drinking vinegar “Ringo Su” (apple vinegar)(manufactured by Mizkan Co., Ltd.) was diluted with 5.25-fold amount ofwater, and the sample obtained in Example 20 which was derived fromorange juice was added thereto to a concentration of 10,000 ppm toprepare a sample solution of Example 21. Further, for comparison, therewere prepared a sample solution of Comparative Example 19 by adding theraw concentrated orange juice to the diluted Ringo Su to a concentrationof 21,500 ppm and a sample solution of Comparative Example 20 by addinga 1% hesperidin mixture solution (hesperidin (manufactured by TCI): αGhesperidin (manufactured by Toyo Sugar Refining Co., Ltd.) =3:7) to thediluted Ringo Su to a concentration of 10,000 ppm.

For examining difference between the sample solution of Example 21 andthe comparative sample solution by sensory evaluation, 9 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which orange juice was added, 3 out of 9 panelists evaluatedas “weak sourness-suppressing effect being recognized” and 6 panelistsevaluated as “no effects being recognized”. With the sample solution towhich the hesperidin mixture solution was added, 3 out of 9 panelistsevaluated as “weak sourness-suppressing effect being recognized”, and 6evaluated as “no effects being recognized”. On the other hand, with thesample solution of Example 21, 8 out of 9 panelists evaluated as “strongsourness-suppressing effect being recognized” and 1 panelist evaluatedas “weak sourness-suppressing effect being recognized”, thus nopanelists evaluating the sample solution of Example 21 as “no effectsbeing recognized”. Results are shown in Table 11.

TABLE 11 Flavor improving Suppression effect of sourness agent StrongWeak No effects Example 21 Fraction derived 8 1 0 from orange juiceComparative Orange juice 0 3 6 Example 19 Comparative Hesperidin mixture0 3 6 Example 20

From the above-described results, it has become apparent that thefraction of Example 20 derived from orange juice has the effect ofreducing sourness of apple vinegar.

Example 22 Preparation of Flavor Improving Agent Derived from Pear Juice

248 g of water was added to 433 g of concentrated pear juice (Bx. 70.5)to dilute. The water-diluted pear juice obtained had Bx. 45.0. Thediluted fruit juice was allowed to pass at a flow rate of SV=1 through acolumn (column size: inner diameter: 5 cm; height: 23 cm) filled with300 g of DIAION HP20 (manufactured by Mitsubishi Chemical). Aftercompletion of the pass-through operation, 2600 g of water was allowed topass through the column at SV=5 for washing. Next, 700 g of a 92%ethanol aqueous solution was allowed to pass through the column at SV=3to thereby elute adsorbed ingredients. 690 g of the thus-obtained eluatewas referred to as a sample of flavor improving agent (solid content:0.18%) derived from pear juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.462 mmol andthat of the sample to be 0.245 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 162 mmol and that of the sampleto be 0.00653 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00285 and the sample was found to havePP/SG before hydrolysis of 37.5. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw material was found to be 162 mmol and that of thesample was found to be 0.107 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00285, and thesample was found to have PP/SG after hydrolysis of 2.29.

Example 23 and Comparative Examples 21 and 22 Suppression of Sourness ofCitric Acid Aqueous Solution

Citric acid anhydride (manufactured by Junsei Chemical Co., Ltd.) wasdissolved in water to prepare a 0.4% aqueous solution thereof. Thesample obtained in Example 22 which was derived from pear juice wasadded thereto to a concentration of 100 ppm to prepare a sample solutionof Example 23. Further, for comparison, there were prepared a samplesolution of Comparative Example 21 by adding the raw concentrated pearjuice to the citric acid aqueous solution to a concentration of 65 ppmand a sample solution of Comparative Example 22 by adding a 1%hesperidin mixture solution (hesperidin (manufactured by TCI): αGhesperidin (manufactured by Toyo Sugar Refining Co., Ltd.) =3:7) to thecitric acid aqueous solution to a concentration of 100 ppm.

For examining difference between the sample solutions of Example 23 andthe comparative sample solutions by sensory evaluation, 8 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which pear juice was added, 3 out of 8 panelists evaluatedas “weak sourness-suppressing effect being recognized” and 5 panelistsevaluated as “no effects being recognized”. With the sample solution towhich the hesperidin mixture solution was added, 2 out of 8 panelistsevaluated as “weak sourness-suppressing effect being recognized”, and 6evaluated as “no effects being recognized”. On the other hand, with thesample solution of Example 23, 6 out of 8 panelists evaluated as “strongsourness-suppressing effect being recognized” and 2 panelists evaluatedas “weak sourness-suppressing effect being recognized”, thus nopanelists evaluating the sample solution of Example 23 as “no effectsbeing recognized”. Results of these are shown in Table 12.

TABLE 12 Flavor improving Suppression effect of sourness agent StrongWeak No effects Example 23 Fraction derived 6 2 0 from pear juiceComparative Pear juice 0 3 5 Example 21 Comparative Hesperidin mixture 02 6 Example 22

From the above-described results, it has become apparent that thefraction of Example 22 derived from pear juice has the effect ofreducing sourness of citric acid.

Example 24 Preparation of Flavor Improving Agent Derived from BananaJuice

350 g of water was added to 213 g of banana concentrated cloudy juice(Bx. 22.7; manufactured by Nankai Kako K.K.) to dilute. This dilutedfruit juice was mixed with 25 g of Celite 545, followed by suctionfiltration to obtain 500 g of a diluted fruit juice (8.6 Bx.) from whichfibrous substances were removed. This juice was allowed to pass at aflow rate of SV=4 through a column (column size: inner diameter: 3 cm;height: 10.4 cm) filled with 50 g of DIAION HP20 (manufactured byMitsubishi Chemical). After completion of the pass-through operation,440 g of water was allowed to pass through the column at SV=4 forwashing. Next, 190 g of a 74% ethanol aqueous solution was allowed topass through the column at SV=4 to thereby elute adsorbed ingredients.190 g of the thus-obtained eluate was mixed with 2 g of Celite 545,followed by suction filtration. 175 g of the thus-obtained eluate wasreferred to as a sample of flavor improving agent (solid content: 0.12%)derived from banana juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.274 mmol andthat of the sample to be 0.0800 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 34.1 mmol and that of the sampleto be 0.00286 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00804, and the sample was found tohave PP/SG before hydrolysis of 28.0. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis according to theaforementioned predetermined method, the amount of sugar of the rawmaterial was found to be 34.3 mmol and that of the sample was found tobe 0.0486 mmol. From these results, the raw fruit juice was found tohave PP/SG after hydrolysis of 0.00799 and the sample was found to havePP/SG after hydrolysis of 1.65.

Example 25 and Comparative Example 23 Effect of Giving a Richness

5.3 g of a dry solid soup “Ajinomoto kk konsome (consommé) (block type)”(manufactured by Ajinomoto Co., Inc.) was dissolved in 300 ml of hotwater to prepare a solution. The sample obtained in Example 24 which wasderived from banana juice was added to the solution to a concentrationof 100 ppm to prepare a sample solution of Example 25. Further, forcomparison, a comparative sample solution of Comparative Example 23 wasprepared by adding the raw concentrated banana juice to the soup to aconcentration of 120 ppm.

For examining difference between the sample solution of Example 25 andthe comparative sample solution by sensory evaluation, 9 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which banana juice was added, 2 out of 9 panelists evaluatedas “weak effect of giving a richness being recognized” and 7 panelistsevaluated as “no effects being recognized”. On the other hand, with thesample solution of Example 25, 9 out of 9 panelists evaluated as “strongeffect of giving a richness being recognized”, thus no panelistsevaluating the sample solution of Example 25 as “no effects beingrecognized”. Results are shown in Table 13.

TABLE 13 Flavor improving Effect of giving a richness agent Strong WeakNo effects Example 25 Fraction derived 9 0 0 from banana juiceComparative Banana juice 0 2 7 Example 23

From the above-described results, it has become apparent that thefraction of Example 24 derived from banana juice has the effect ofgiving a richness.

Example 26 Preparation of Flavor Improving Agent Derived from LemonJuice

250 g of concentrated lemon juice (Bx. 43.2; manufactured by CIS SICILY)was allowed to pass at a flow rate of SV-1 through a column (columnsize: inner diameter: 5 cm; height: 15 cm) filled with 200 g of DIAIONHP20 (manufactured by Mitsubishi Chemical). After completion of thepass-through operation, 1,500 g of water was allowed to pass though thecolumn at SV-5 for washing. Next, 500 g of a 74% ethanol aqueoussolution was allowed to pass though the column at SV=2 to thereby eluteadsorbed ingredients. 500 g of the thus-obtained eluate (solid content:0.22%) was referred to as a sample of flavor improving agent derivedfrom lemon juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.288 mmol andthat of the sample to be 0.0956 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 65.4 mmol and that of the sampleto be 0.00500 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00440 and the sample was found to havePP/SG before hydrolysis of 19.1. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw fruit juice was found to be 65.8 mmol and that of thesample was found to be 0.109 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00438 and the samplewas found to have PP/SG after hydrolysis of 0.877.

Example 27 and Comparative Example 24 Effect of Giving a Juice-Like Feel

Water was added to 214 g of high fructose corn syrup and 2.6 g of citricacid to prepare 400 g of an aqueous solution and, further, 1,600 g ofcarbonated water and 2 g of an apple flavor were added thereto toprepare a material. The sample obtained in Example 26 which was derivedfrom lemon juice was added to this material to a concentration of 1,800ppm to prepare a sample solution of Example 27. Further, for comparison,a sample solution of Comparative Example 24 was prepared by adding theraw apple juice to the material to a concentration of 900 ppm.

For examining difference between the sample solution of Example 27 andthe comparative sample solution by sensory evaluation, 10 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which lemon juice was added, 3 out of 10 panelists evaluatedas “weak effect of giving a juice-like feel being recognized” and 7panelists evaluated as “no effects being recognized”. On the other hand,with the sample solution of Example 27, 8 out of 10 panelists evaluatedas “strong effect of giving a juice-like feel being recognized” and 2panelists evaluated as “weak effect of giving a juice-like feel beingrecognized”, thus no panelists evaluating the sample solution of Example27 as “no effects being recognized”. Results are shown in Table 14.

TABLE 14 Flavor improving Effect of giving a juice-like feel agentStrong Weak No effects Example 27 Fraction derived 8 2 0 from lemonjuice Comparative Lemon juice 0 3 7 Example 24

From the above-described results, it has become apparent that thefraction of Example 26 derived from lemon juice has the effect of givinga juice-like feel.

Example 28 Preparation of Flavor Improving Agent Derived from Lime Juice

250 g of water was added to 180 g of concentrated lime juice (Bx. 44.3;manufactured by CIS SICILY) to dilute. The water-diluted pear juiceobtained had Bx. 18.5. The diluted fruit juice was allowed to pass at aflow rate of SV=5 through a column (column size: inner diameter: 5 cm;height: 7.5 cm) filled with 100 g of DIAION HP20 (manufactured byMitsubishi Chemical). After completion of the pass-through operation,880 g of water was allowed to pass through the column at SV=5 forwashing. Next, 240 g of a 92% ethanol aqueous solution was allowed topass through the column at SV=2 to thereby elute adsorbed ingredients.240 g of the thus-obtained eluate (solid content: 0.17%) was referred toas a sample of flavor improving agent derived from lime juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.247 mmol andthat of the sample to be 0.160 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method, and the sugaramount of the raw fruit juice was found to be 71.1 mmol and that of thesample to be 0.0167 mmol. From these results, the raw fruit juice wasfound to have PP/SG before hydrolysis of 0.00347 and the sample wasfound to have PP/SG before hydrolysis of 9.58. Also, as a result ofmeasuring the sugar amount in the same manner after acid hydrolysis, theamount of sugar of the raw fruit juicel was found to be 71.2 mmol andthat of the sample was found to be 0.133 mmol. From these results, theraw fruit juice was found to have PP/SG after hydrolysis of 0.00347 andthe sample was found to have PP/SG after hydrolysis of 1.20.

Example 29 and Comparative Examples 25 and 26 Effect of SuppressingHarsh Taste of Vegetables

The sample obtained in Example 28 which was derived from lime juice wasadded to commercially available green juice “Super Aojiru” (manufacturedby Fancl Corporation) to a concentration of 15,000 ppm to prepare asample solution of Example 29. Further, for comparison, there wereprepared a sample solution of Comparative Example 25 by adding the rawconcentrated lime juice to Super Aojiru to a concentration of 11,500 ppmand a sample solution of Comparative Example 26 by adding a 1%hesperidin mixture solution (hesperidin (manufactured by TCI): αGhesperidin (manufactured by Toyo Sugar Refining Co., Ltd.) =3:7) toSuper Aojiru to a concentration of 15,000 ppm.

For examining difference between the sample solution of Example 29 andthe comparative sample solutions by sensory evaluation, 10 panelistswere asked to compare these by drinking. As a result, with the samplesolution to which lime juice was added, 3 out of 10 panelists evaluatedas “weak harsh taste-suppressing effect being recognized” and 7panelists evaluated as “no effects being recognized”. With the samplesolution to which the hesperidin mixture solution was added, 4 out of 10panelists evaluated as “weak harsh taste-suppressing effect beingrecognized” and 6 evaluated as “no effects being recognized”. On theother hand, with the sample solution of Example 29, 7 out of 10panelists evaluated as “strong harsh taste-suppressing effect beingrecognized” and 3 panelists evaluated as “weak harsh taste-suppressingeffect being recognized”, thus no panelists evaluating the samplesolution of Example 29 as “no effects being recognized”. Results areshown in Table 15.

TABLE 15 Flavor improving Suppression effect of harsh taste agent StrongWeak No effects Example 29 Fraction derived 7 3 0 from lime juiceComparative Lime juice 0 3 7 Example 25 Comparative Hesperidin mixture 04 6 Example 26

From the above-described results, it has become apparent that thefraction of Example 28 derived from lime juice has the effect ofreducing harsh taste of vegetables.

Example 30 Preparation of Flavor Improving Agent Derived from GrapefruitJuice

250 g of water was added to 200 g of concentrated grapefruit juice (Bx.54.1; manufactured by CIS SICILY) to dilute. The water-dilutedgrapefruits juice obtained had Bx. 24.0. The diluted fruit juice wasallowed to pass at a flow rate of SV=3 through a column (column size:inner diameter: 5 cm; height: 7.5 cm) filled with 100 g of DIAION HP20(manufactured by Mitsubishi Chemical). After completion of thepass-through operation, 880 g of water was allowed to pass through thecolumn at SV-5 for washing. Next, 250 g of a 74% ethanol aqueoussolution was allowed to pass through the column at SV-2 to thereby eluteadsorbed ingredients. 250 g of the thus-obtained eluate (solid content:0.19%) was referred to as a sample of flavor improving agent derivedfrom grapefruit juice.

Polyphenol amounts in terms of chlorogenic acid in each 50 g of the rawfruit juice and the obtained sample were measured and, as a result, thepolyphenol amount of the raw fruit juice was found to be 0.337 mmol andthat of the sample to be 0.204 mmol. Then, sugar amounts were measuredaccording to the aforementioned predetermined method. The sugar amountof the raw fruit juice was found to be 61.4 mmol and that of the sampleto be 0.0100 mmol. From these results, the raw fruit juice was found tohave PP/SG before hydrolysis of 0.00549 and the sample was found to havePP/SG before hydrolysis of 20.4. Also, as a result of measuring thesugar amount in the same manner after acid hydrolysis, the amount ofsugar of the raw fruit juice was found to be 61.7 mmol and that of thesample was found to be 0.174 mmol. From these results, the raw fruitjuice was found to have PP/SG after hydrolysis of 0.00546 and the samplewas found to have PP/SG after hydrolysis of 1.17.

Example 31 and Comparative Examples 27 and 28 Effect of SuppressingBitterness of Caffeine

Anhydrous caffeine (manufactured by NACALAI TESQUE, INC.) was dissolvedin water to prepare a 0.04% caffeine aqueous solution. The sampleobtained in Example 30 which was derived from grapefruit juice was addedto the aqueous solution to a concentration of 100 ppm to prepare asample solution of Example 31. Further, for comparison, there wereprepared a sample solution of Comparative Example 27 by adding the rawconcentrated grapefruit juice to a concentration of 80 ppm and a samplesolution of Comparative Example by adding a 1% hesperidin mixturesolution (hesperidin (manufactured by TCI): αG hesperidin (manufacturedby Toyo Sugar Refining Co., Ltd.) =3:7) to a concentration of 100 ppm.

For examining difference between the sample solution of Example 31 andthe comparative sample solutions by sensory evaluation, 7 panelists wereasked to compare these by drinking. As a result, with the samplesolution to which raw grapefruit juice was added, 3 out of 7 panelistsevaluated as “weak bitterness-suppressing effect being recognized” and 4panelists evaluated as “no effects being recognized”. With the samplesolution to which the hesperidin mixture solution was added, 3 out of 7panelists evaluated as “weak bitterness-suppressing effect beingrecognized” and 4 evaluated as “no effects being recognized”. On theother hand, with the sample solution of Example 31, 5 out of 7 panelistsevaluated as “strong bitterness-suppressing effect being recognized”,and 2 panelists evaluated as “weak bitterness-suppressing effect beingrecognized”, thus no panelists evaluating the sample solution of Example31 as “no effects being recognized”. Results are shown in Table 16.

TABLE 16 Flavor improving Suppression effect of bitterness agent StrongWeak No effects Example 31 Fraction derived 5 2 0 from grapefruit juiceComparative Grapefruit juice 0 3 4 Example 27 Comparative Hesperidinmixture 0 3 4 Example 28From the above-described results, it has become apparent that thefraction of Example 30 derived from grapefruit juice has the effect ofreducing bitterness.

1. A flavor improving agent comprising a fraction derived from fruitjuice or squeeze, wherein the amount of substance ratio betweenpolyphenols and saccharides, the latter after acid hydrolysis of thefraction, (polyphenol/saccharide) is 0.1 to
 10. 2. The flavor improvingagent according to claim 1, wherein the amount of substance ratiobetween polyphenols and saccharides before acid hydrolysis of thefraction, (polyphenol/saccharide) is 1 to
 100. 3. The flavor improvingagent according to claim 1 or 2, wherein the fraction is obtained byadsorbing fruit juice or squeeze onto a synthetic resin adsorbent, andeluting the adsorbed ingredients with a solvent.
 4. The flavor improvingagent according to claim 1 or 2, wherein the fraction is an ethanolextract of fruit juice or squeeze.
 5. The flavor improving agentaccording to claim 1 or 2, wherein the fruit is one member selected fromamong orange, lemon, grapefruit, lime, blueberry, strawberry, apple,pear, grape, melon, pineapple, peach, mango, and banana.
 6. The flavorimproving agent according to claim 1 or 2, wherein the flavor improvingeffect is at least one of suppressing sourness, bitterness orastringency, reducing harsh taste of vegetables, giving juice-like feel,and giving a richness.
 7. A flavor composition containing a flavorimproving agent according to claim 1 or
 2. 8. Foods and beveragescontaining a flavor improving agent according to claim 1 or
 2. 9. Apharmaceutical product containing a flavor improving agent according toclaim 1 or
 2. 10. An oral care product containing a flavor improvingagent according to claim 1 or 2.